Is that our aim?
Long ago, I used to work for market makers. These days, I do a lot of work for Internet companies. In both lines of work, risk management is essential. In both, the aim is to take as many well-managed, likely-profitable risks as possible. That's how things get better, and that's where a lot of your best information comes from.
The risk management strategy you describe strikes me as a good one for something much more settled, like a water utility.
Do you really think Wikipedia should be that risk-averse? I had thought it a much more dynamic enterprise, at least for the next few decades.
Risk management is always about balancing risk and reward. How risk-averse you are determines where you put that balance (in other words, how much reward you require to make the risk worthwhile), but you have to put the balance somewhere. It's never wise to take a risk that offers no reward. Being not at all averse to risk is never a good idea.